STEROIDAL HETEROCYCLES. X. STEROIDAL(3,2-D)PYRIMIDINES AND RELATED COMPOUNDS.
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With 4-oxo-4,5,6,7-tetrahydrobenzothiophene and 2-methyl-3-oxothiophane-1-dioxide (III) as AB and D ring precursors respectively, (+/-)-3,17-dithia-A-nor-14 beta-estra-1,5(10),6,8-tetraene-17-dioxide (I) was synthesised following the modified Torgov method.
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2-Methyl-3-oxothiophane-1-dioxide (II) was prepared and was used as the D ring precursor in the total synthesis of the title compound via modified Torgov synthesis.
With 7-hydroxy-7a-methyl-4-oxo-cyclopenta(b)tetrahydrothiopyran-1-dioxide (III) as the CD part, the synthesis of the title compound (II) was achieved by the Fischer indole synthesis.
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The total synthesis of (+/-)-8,13-diaza-3-thia-A-norgona-1,5(10)-dien-17-one (XII) was achieved starting from 2-(2-thienyl) ethylamine (VII) and 3-succinimidopropionyl chloride (IX) as the A and D ring precursors respectively.
1-Oxo-4-oxa-1,2,3,4-tetrahydrophenanthrene is converted into racemic benz[3,4]-6-oxaestra-1,3,5(10),8-tetraen-17 beta-ol in 45% yield.
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